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Diethyl maleate

Diethyl maleate structure

CAS No:
141-05-9
Formula:
C8H12O4
Chemical Name:
Diethyl maleate
Synonyms:
2-Butenedioic acid (2Z)-,1,4-diethyl ester;Maleic acid,diethyl ester;2-Butenedioic acid (Z)-,diethyl ester;2-Butenedioic acid (2Z)-,diethyl ester;Diethyl maleate;Ethyl maleate;Diethyl (Z)-2-butenedioate;Staflex DEM;(2Z)-2-Butenedioic acid diethyl ester;Maleinic acid diethyl ester;(Z)-2-Butenedioic acid diethyl ester
Categories:
Agrochemicals > Pesticide Intermediates

Description

Liquid

Diethyl maleate is a maleate ester resulting from the formal condensation of both carboxy groups of maleic acid with ethanol. A colourless liquid at room temperature (m.p. -10℃) with boiling point 220℃ at 1 atm., it is commonly used as a dienophile for Diels-Alder-type cycloaddition reactions in organic synthesis. It has a role as a glutathione depleting agent. It is a maleate ester and an ethyl ester. It derives from an ethanol.

Diethyl maleate Basic Attributes

Molecular Weight：

172.18

Exact Mass：

172.18

BRN：

1100825

EC Number：

205-451-9

UNII：

G81WQB56OL

NSC Number：

8394

DSSTox ID：

DTXSID8020464

HScode：

29171990

Characteristics

PSA：

52.6

XLogP3：

1.68

Appearance：

Clear Liquid

Density：

1.0690 g/cm³ @ Temp: 20 °C

Melting Point：

-8.8 °C

Boiling Point：

223 °C

Flash Point：

200 °F

Refractive Index：

1.443

Water Solubility：

H2O: insoluble

Storage Conditions：

Store below +30°C.

Vapor Pressure：

1 mm Hg ( 14 °C)

Vapor Density：

5.93 (vs air)

Safety Information

Transport codes：

3334

wgk germany：

hazard class code：

36-43-52/53

safety instructions：

26-36/37-37-24-24/25

RTECS Number：

ON1225000

Marks：

Stability/Shelf Life：

Stable. Combustible. Incompatible with oxidizing agents, bases, acids, reducing agents.

Precautionary statement(s)：

P273-P280-P305 + P351 + P338

Hazard Statements：

H317-H319-H412

GHS Classification：

|Warning|H317 (99.03%): May cause an allergic skin reaction [Warning Sensitization, Skin]|P261, P264, P272, P273, P280, P302+P352, P305+P351+P338, P321, P333+P313, P337+P313, P363, and P501|Aggregated GHS information provided by 212 companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Drug Information

MeSH Entry Terms：

diethyl maleate

Diethyl maleate Use and Manufacturing

Methods of Manufacturing

The preparation method is mainly prepared by esterification of maleic anhydride and ethanol in the presence of sulfuric acid. This process has two kinds of phenyl esterification under normal pressure and non-phenyl esterification under negative pressure. (1) At normal pressure, there is benzene esterification. A certain amount of benzene and ethanol are added to the esterification reaction pot, maleic anhydride is added, concentrated sulfuric acid is added dropwise with stirring, and the jacket steam is heated to make the reactant at about 75 ℃ Carry out the esterification reaction. The generated water, benzene and ethanol are removed by ternary azeotropic distillation, and the upper layer of benzene and ethanol liquid is returned to the reactor. After about 13-14 hours, when the temperature of the top of the distillation tower rose to 68.2°C and the water level of the lower layer of the separator no longer rose, it indicated that all the water in the reaction pot had been distilled off and the esterification reaction was completed. Stop reflux, continue to distill to 95～100℃, distill out benzene and ethanol. Cooling down to about 50 ℃, neutralizing treatment with 5% sodium carbonate aqueous solution, washing with water and then removing residual benzene and ethanol in vacuum to obtain the product diethyl maleate. (2) Negative pressure non-phenyl esterified maleic anhydride and ethanol are esterified under the action of sulfuric acid. Under certain vacuum and temperature, the ethanol and the water produced by the reaction are taken out in a gaseous state, and then the ethanol is separated and refluxed through a fractionation tower Esterification makes the reaction complete. This method can shorten the reaction cycle, improve the yield and product quality, and improve the operating environment. Most domestic manufacturers use this method. In addition, cation exchange resin can also be used as a catalyst for exchange conversion to prepare diethyl maleate.

Uses

In organic synthesis.

Adhesives and sealant chemicals

Agricultural products (non-pesticidal)

Manufacturing Info：

Food, beverage, and tobacco product manufacturing|2-Butenedioic acid (2Z)-, 1,4-diethyl ester: ACTIVE

Use Classification：

Food additives -> Flavoring Agents

Food Additive Classes：

Flavoring Agents

Computed Properties

Molecular Weight:172.18
XLogP3:0.9
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:6
Exact Mass:172.07355886
Monoisotopic Mass:172.07355886
Topological Polar Surface Area:52.6
Heavy Atom Count:12
Complexity:164
Defined Bond Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Material

Maleic anhydride

Ethanol

α-Methylstyrene

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